From GovTech to Entrepreneurship: A 15-Year Journey
I’ve worked in GovTech for the better part of 15 years, primarily in software engineering, data science, and cybersecurity. Throughout my career, I’ve started a number of side projects, not to take them to market, but to teach myself new skills that I could bring back into my day job.
Family, Timing, and the Move Back to Missouri
Recently, my wife and I started a family. At the time of writing this, we have two young boys, one 14 months old and the other 2 months old. While we didn’t plan to have them so close together, we now see it as a blessing: they’ll get to grow up alongside each other.
For years, I considered moving back to Missouri to be closer to family, but I struggled with the idea of walking away from a career I had been building for nearly two decades. The birth of our first son in May 2024 shifted my mindset from “Is this the right time?” to “How can we make this work?”
Buying a House, Reassessing My Career, and Exploring Acquisitions
In October 2024, we flew to Missouri for a family reunion. During that trip, my wife and I toured a home that we ended up purchasing in December 2024. At the time, I thought I would be able to go fully remote in my GovTech role. But as we approached the closing, I started asking myself a bigger question:
What if I’m done with GovTech? What do I want to do next?
That question led me down the rabbit hole of business acquisition. I began listening to podcasts, reading blogs, and learning everything I could about buying small online businesses, especially SaaS products. Given my background in software and data science, it felt like a natural next step.
Discovering the World of Digital Asset Acquistions
I started reviewing listings on platforms like:
I signed NDAs, dug into financials, and learned how to evaluate deal quality. It quickly became clear that financing digital assets is harder than buying physical businesses, especially when banks don’t recognize SaaS revenue as collateral. Still, I kept looking for a path forward.
I Had Close to Half a Million in Retirement Funds, But How Could I Use It Without Penalty?
As a frugal professional, I had built up a sizable 401(k) and TSP account over the years. I started running the numbers: I wanted to deploy $300K into acquisitions… but the penalties and taxes for early withdrawal were brutal.
That’s when I discovered ROBS—Rollover for Business Startups.
What Is a ROBS and How Does It Work?
ROBS is an IRS-compliant structure that allows entrepreneurs to invest retirement funds into a new business without taxes or early withdrawal penalties.
Here’s a high-level breakdown of how it works:
- Create a C-Corporation
- Set up a 401(k) plan under the C-Corp
- Rollover funds from your old retirement account into the new 401(k)
- Use the 401(k) to buy stock in your new C-Corp
- Your C-Corp receives the cash to operate and acquire assets
In my case, I worked with Guidant Financial and used Fidelity as the custodian. The process took some paperwork and planning, but the result was a tax-advantaged way to fund business acquisitions using my existing retirement funds.
The Emotional Risk of Going All-In
As the sole provider for my family, I struggled with the idea of risking our financial future on acquisitions. But ultimately, I realized that if I selected solid businesses, operated them with discipline, and played a long game, I could build something meaningful over the next 3–5 years and potentially replace my 9–5 entirely.
What I’m Working on Now (And What’s Next)
At the time of writing, I’m in the process of closing several acquisitions, primarily SaaS products and blogs. I’ll be documenting those journeys right here on this blog.
I plan to share:
- My experience using ROBS for acquisition
- The due diligence checklists and frameworks I use
- How I grow and operate these businesses part-time while raising a family
- Tools and automation I’m building to scale operations
Final Thoughts
This blog isn’t just about my personal journey, it’s also a playbook for anyone who wants to:
- Transition from W-2 to ownership
- Use retirement funds strategically
- Acquire digital businesses the smart way
If you’re exploring how to buy or operate online businesses—or if you’re curious about using a ROBS structure—stick around. I’ll be sharing every step.
Comments
2 responses
Interesting post! Looking forward to reading about your experience using ROBS, as well as how you grow and operate your businesses while raising your children. Best of luck to you!
Thanks, Thecla for your kind words and always being a supportive big sister, I appreciate you and love you very much!1